JP5291856B2 - オレフィンオリゴマー化 - Google Patents
オレフィンオリゴマー化 Download PDFInfo
- Publication number
- JP5291856B2 JP5291856B2 JP2003538101A JP2003538101A JP5291856B2 JP 5291856 B2 JP5291856 B2 JP 5291856B2 JP 2003538101 A JP2003538101 A JP 2003538101A JP 2003538101 A JP2003538101 A JP 2003538101A JP 5291856 B2 JP5291856 B2 JP 5291856B2
- Authority
- JP
- Japan
- Prior art keywords
- sulfur
- ppm
- feedstock
- oligomerization
- sulfide
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2/00—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms
- C07C2/02—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons
- C07C2/04—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation
- C07C2/06—Preparation of hydrocarbons from hydrocarbons containing a smaller number of carbon atoms by addition between unsaturated hydrocarbons by oligomerisation of well-defined unsaturated hydrocarbons without ring formation of alkenes, i.e. acyclic hydrocarbons having only one carbon-to-carbon double bond
- C07C2/08—Catalytic processes
- C07C2/12—Catalytic processes with crystalline alumino-silicates or with catalysts comprising molecular sieves
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/10—After treatment, characterised by the effect to be obtained
- B01J2229/18—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself
- B01J2229/186—After treatment, characterised by the effect to be obtained to introduce other elements into or onto the molecular sieve itself not in framework positions
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B01—PHYSICAL OR CHEMICAL PROCESSES OR APPARATUS IN GENERAL
- B01J—CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B01J2229/00—Aspects of molecular sieve catalysts not covered by B01J29/00
- B01J2229/30—After treatment, characterised by the means used
- B01J2229/34—Reaction with organic or organometallic compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C2529/00—Catalysts comprising molecular sieves
- C07C2529/04—Catalysts comprising molecular sieves having base-exchange properties, e.g. crystalline zeolites, pillared clays
- C07C2529/06—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof
- C07C2529/70—Crystalline aluminosilicate zeolites; Isomorphous compounds thereof of types characterised by their specific structure not provided for in groups C07C2529/08 - C07C2529/65
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Crystallography & Structural Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
- Polymerization Catalysts (AREA)
Description
下記の実施例は、本発明を例示し、他に示されていなければ、部及び%は重量による。
供給原料A:48%のプロペン、3%のブテン、4%のエタン、20%のプロパン、9%のn−ブタン、16%のイソブタン及び22.4容量ppmの硫黄含有化合物[3ppmのチオフェン類、2ppmのメルカプタン類(チオール類)、10ppmの硫化ジアルキル類、3ppmの二硫化ジアルキル類、1ppmのH2S、残量は、特定できない硫黄含有種]を含有する市販のプロペン供給原料
供給原料B:保護床による硫黄除去後の供給原料A(硫黄含量<0.1容量ppm)
供給原料C:50%のプロペン、40%のn−ブタン、10%のイソブタンを含有する硫黄非含有(硫黄化合物含量<0.1容量ppm)プロペン供給原料
触媒A:押出H−ZSM−57触媒
触媒B:H−ZSM−57の粉末化試料
触媒C:押出H−ZSM−22触媒
として表わされる。
特定された供給原料を、2時間−1の総供給原料空間速度において、温度は、少なくとも80%のアルケン変換率に達するまで、135℃から上昇させて、触媒A及びB、ZSM−57に通した。二量体への変換率及び選択性を分析し、その結果を表1に示す。
触媒Bでのオリゴマー化の前に、供給原料Cの種々の試料に種々の硫黄化合物を添加した。初期の変換率、操作中の時間とともに変換における低減、ノネンに対する選択性が観察された。その結果を表2に示す。
Claims (7)
- 160℃乃至230℃の温度、5乃至10MPaの範囲の圧力、及び1.5乃至7.5時間 −1 のオレフィンの毎時空間速度を含む、オリゴマー化条件下で、
プロペン、及びブテン類、及び/又はペンテン類を含み、及び硫黄を含む飽和された脂肪族化合物をその容量に基づいて0.1乃至2容量ppm含有する、オレフィン系供給原料を、MFS構造タイプの結晶質分子篩を含有する触媒と接触させること、及び少なくとも1つのオレフィンオリゴマーを含有する生成物を回収することを含み、三量体生成に対する選択性を維持させるか又は増大させることを特徴とする、オレフィン系供給原料のオリゴマー化のための方法。 - オリゴマー化を行なう前に、2容量ppmより多い硫黄を含む飽和された脂肪族化合物を含むオレフィン系供給原料中の硫黄を含む飽和された脂肪族化合物の含量を0.1乃至2容量ppmの含量に低減させることを含む、請求項1に記載の方法。
- MFS構造の結晶質分子篩がH−ZSM−57である、請求項1又は2のいずれかに記載の方法。
- 供給原料が、プロペンを含有する、請求項1、2、及び3のいずれか1請求項に記載の方法。
- 硫黄を含む飽和された脂肪族化合物が、硫化ジメチル、硫化ジエチル、硫化エチルメチル、硫化n−プロピル、n−プロパンチオール、1−ブタンチオール、1,1−メチルエチルチオール、二硫化エチルメチル、二硫化ジメチル及びテトラヒドロチオフェンから選ばれる少なくとも1つの化合物を含有する、請求項1乃至4のいずれか1請求項に記載の方法。
- 請求項1乃至5のいずれか1請求項に記載の方法であって、少なくとも1つのオリゴマーを含む生成物をヒドロホルミル化及び水素化して、アルコールを生成する、方法。
- 前記アルコールを無機酸又は有機酸でエステル化して、エステルを生成する、請求項6の方法
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP01309032.9 | 2001-10-24 | ||
EP01309032 | 2001-10-24 | ||
PCT/GB2002/004771 WO2003035583A1 (en) | 2001-10-24 | 2002-10-23 | Olefin oligomerization |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010228475A Division JP2011042663A (ja) | 2001-10-24 | 2010-10-08 | オレフィンオリゴマー化 |
Publications (3)
Publication Number | Publication Date |
---|---|
JP2005506373A JP2005506373A (ja) | 2005-03-03 |
JP2005506373A5 JP2005506373A5 (ja) | 2006-01-05 |
JP5291856B2 true JP5291856B2 (ja) | 2013-09-18 |
Family
ID=8182391
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2003538101A Expired - Fee Related JP5291856B2 (ja) | 2001-10-24 | 2002-10-23 | オレフィンオリゴマー化 |
JP2010228475A Withdrawn JP2011042663A (ja) | 2001-10-24 | 2010-10-08 | オレフィンオリゴマー化 |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2010228475A Withdrawn JP2011042663A (ja) | 2001-10-24 | 2010-10-08 | オレフィンオリゴマー化 |
Country Status (9)
Country | Link |
---|---|
US (2) | US7247763B2 (ja) |
EP (1) | EP1438276B1 (ja) |
JP (2) | JP5291856B2 (ja) |
CN (1) | CN100425581C (ja) |
AR (1) | AR036902A1 (ja) |
AT (1) | ATE464277T1 (ja) |
DE (1) | DE60236009D1 (ja) |
WO (1) | WO2003035583A1 (ja) |
ZA (1) | ZA200402836B (ja) |
Families Citing this family (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
AR036902A1 (es) * | 2001-10-24 | 2004-10-13 | Exxonmobil Chem Patents Inc | Un proceso para la oligomerizacion de un material de alimentacion olefinico, usos de un limite en el nivel de azufre en el material de alimentacion, una mezcla oligomerica olefinica, y un ester o una composicion polimerica plastificada |
GB0412151D0 (en) | 2004-06-01 | 2004-06-30 | Exxonmobil Chem Patents Inc | Olefin oligomerization process |
GB0412139D0 (en) * | 2004-06-01 | 2004-06-30 | Exxonmobil Chem Patents Inc | Olefin oligomerization process |
US20100144514A1 (en) * | 2008-12-09 | 2010-06-10 | Nicholas Christopher P | Process for Making Catalyst for Olefin Upgrading |
US20100144513A1 (en) * | 2008-12-09 | 2010-06-10 | Nicholas Christopher P | Catalyst for Olefin Upgrading |
EP2513153A1 (en) | 2009-12-15 | 2012-10-24 | ExxonMobil Chemical Patents Inc. | Temperature control of an oligomerisation process and reactor |
US20140135553A1 (en) * | 2012-11-12 | 2014-05-15 | Uop Llc | Process for recycling oligomerate to oligomerization |
EP3867212A4 (en) * | 2018-10-17 | 2022-08-31 | ExxonMobil Chemical Patents Inc. | OLEFIN OLIGOMERIZATION |
WO2021075267A1 (ja) * | 2019-10-18 | 2021-04-22 | 出光興産株式会社 | プロピレンオリゴマーの製造方法 |
Family Cites Families (26)
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US2778859A (en) * | 1953-05-27 | 1957-01-22 | Exxon Research Engineering Co | Sulfur-free oxo alcohols |
US3527838A (en) * | 1969-01-13 | 1970-09-08 | Shell Oil Co | Ethylene oligomerization |
US4098684A (en) * | 1976-11-29 | 1978-07-04 | Gulf Research & Development Company | Purification of liquid n-paraffins containing carbonyl sulfide and other sulfur compounds |
US4390413A (en) | 1979-12-26 | 1983-06-28 | Chevron Research Company | Hydrocarbon upgrading process |
US4423269A (en) * | 1981-09-25 | 1983-12-27 | Chevron Research Company | Oligomerization of gaseous olefins |
US4456781A (en) * | 1983-04-26 | 1984-06-26 | Mobil Oil Corporation | Catalytic conversion system for oligomerizing olefinic feedstock to produce heavier hydrocarbons |
US4556477A (en) * | 1984-03-07 | 1985-12-03 | Mobil Oil Corporation | Highly siliceous porous crystalline material ZSM-22 and its use in catalytic dewaxing of petroleum stocks |
BR8504010A (pt) | 1984-08-21 | 1986-06-10 | Mobil Oil Corp | Processo para preparacao de zeolito cristalino poroso sintetico e processo para efetuar conversao catalitica de carga organica |
JPH0429136Y2 (ja) * | 1988-07-11 | 1992-07-15 | ||
DE69012295T2 (de) * | 1989-11-16 | 1995-01-05 | Mobil Oil Corp | Verfahren zur Qualitätserhöhung von Leichtolefinströmen. |
US5157201A (en) * | 1990-06-22 | 1992-10-20 | Exxon Chemical Patents Inc. | Process for adsorbing sulfur species from propylene/propane using regenerable adsorbent |
AU663056B2 (en) | 1990-07-27 | 1995-09-28 | Exxon Chemical Patents Inc. | Hydrocarbon treatment |
US5167797A (en) | 1990-12-07 | 1992-12-01 | Exxon Chemical Company Inc. | Removal of sulfur contaminants from hydrocarbons using n-halogeno compounds |
US5672800A (en) | 1992-01-30 | 1997-09-30 | Exxon Chemical Patents Inc. | Alkene oligomerization |
DE69318553T2 (de) * | 1992-06-05 | 1998-12-10 | Exxon Chemical Patents Inc | Zsm 22 zeolith |
GB9225183D0 (en) * | 1992-12-02 | 1993-01-20 | British Petroleum Co Plc | Process for the production of branched olefins |
DE69507598T2 (de) | 1994-02-22 | 1999-09-02 | Exxon Chemical Patents Inc | Oligomerisierung und katalysator dafuer |
DE19629906A1 (de) | 1996-07-24 | 1998-01-29 | Huels Chemische Werke Ag | Verfahren zur Herstellung von Butenoligomeren aus Fischer-Tropsch-Olefinen |
US5965104A (en) | 1996-12-31 | 1999-10-12 | Chevron U.S.A. Inc. | Zeolite SSZ-43 |
BR0109793A (pt) * | 2000-04-03 | 2004-02-10 | Chevron Usa Inc | Processo integrado para preparar isoolefinas a partir de gás de sìntese e composição combustìvel destilada |
US6653514B1 (en) | 2000-05-08 | 2003-11-25 | Shell Oil Company | Removal of phosphorus-containing impurities from an olefin feedstock |
US6566565B1 (en) | 2000-05-08 | 2003-05-20 | Shell Oil Company | Process for preparation of selectively branched detergent products |
US6492568B1 (en) | 2000-05-08 | 2002-12-10 | Shell Oil Company | Removal of phosphorus-containing compounds from an olefin feedstock |
AR036902A1 (es) * | 2001-10-24 | 2004-10-13 | Exxonmobil Chem Patents Inc | Un proceso para la oligomerizacion de un material de alimentacion olefinico, usos de un limite en el nivel de azufre en el material de alimentacion, una mezcla oligomerica olefinica, y un ester o una composicion polimerica plastificada |
US7012167B2 (en) | 2003-10-08 | 2006-03-14 | Lyondell Chemical Technology, L.P. | Diisobutylene process |
CN1894183B (zh) | 2003-12-18 | 2010-09-08 | 埃克森美孚化学专利公司 | 氢化或相关方面的改进 |
-
2002
- 2002-10-21 AR ARP020103957A patent/AR036902A1/es unknown
- 2002-10-23 CN CNB028211197A patent/CN100425581C/zh not_active Expired - Fee Related
- 2002-10-23 AT AT02801958T patent/ATE464277T1/de not_active IP Right Cessation
- 2002-10-23 WO PCT/GB2002/004771 patent/WO2003035583A1/en active Application Filing
- 2002-10-23 US US10/492,706 patent/US7247763B2/en not_active Expired - Fee Related
- 2002-10-23 EP EP02801958A patent/EP1438276B1/en not_active Expired - Lifetime
- 2002-10-23 JP JP2003538101A patent/JP5291856B2/ja not_active Expired - Fee Related
- 2002-10-23 DE DE60236009T patent/DE60236009D1/de not_active Expired - Lifetime
-
2004
- 2004-04-15 ZA ZA2004/02836A patent/ZA200402836B/en unknown
-
2007
- 2007-06-18 US US11/820,135 patent/US7420096B2/en not_active Expired - Fee Related
-
2010
- 2010-10-08 JP JP2010228475A patent/JP2011042663A/ja not_active Withdrawn
Also Published As
Publication number | Publication date |
---|---|
CN100425581C (zh) | 2008-10-15 |
ZA200402836B (en) | 2005-02-23 |
CN1575267A (zh) | 2005-02-02 |
ATE464277T1 (de) | 2010-04-15 |
US20050020865A1 (en) | 2005-01-27 |
WO2003035583A1 (en) | 2003-05-01 |
US20070260020A1 (en) | 2007-11-08 |
EP1438276A1 (en) | 2004-07-21 |
US7247763B2 (en) | 2007-07-24 |
JP2011042663A (ja) | 2011-03-03 |
DE60236009D1 (de) | 2010-05-27 |
AR036902A1 (es) | 2004-10-13 |
JP2005506373A (ja) | 2005-03-03 |
EP1438276B1 (en) | 2010-04-14 |
US7420096B2 (en) | 2008-09-02 |
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